


Business and Pleasure: Another hit

by Cagedandfree



Series: Sam's Pleasure Buisness [2]
Category: Supernatural
Genre: ABDL, Age Play, Alternate Universe - College/University, Anal Fingering, Anal Plug, Bisexual Sam Winchester, CG/L, Diaper Sex, Diapers, Dom Sam Winchester, Dom/sub, Enemas, F/M, Latex Gloves, Medical Kink, Pullups, Suppository, Vaginal Fingering, Vibrators, i'll add more later, rectal thermometer
Language: English
Status: Completed
Published: 2019-10-27
Updated: 2019-11-24
Packaged: 2021-01-04 15:44:07
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 2,971
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21200099
Author URL: https://archiveofourown.org/users/Cagedandfree/pseuds/Cagedandfree
Summary: Sam Winchester needs to pay for books for school so he offers his services. He has his brother, but he got another hit.This is Molly's story for request.





	1. Littlemedfet

**Author's Note:**

> Sorry this took so long. I will be back at writing!

Sam got a hit on his add someone by the name littlemedfet. They talked for a bit and he learned that she was into medical fetish, but also wearing diapers and pullups. Sam had never thought about that, but it was something he was willing to try. 

He bought the supplies he needed for Molly. That was her name. He dressed in navy blue scrubs and when there was a light knock on the door he went and opened it. There stood Molly, a petite, redhead with green eyes. She was 5’0 nothing which Sam smiled to himself because she would be easy to lift up and hold. 

“Hi sweetie” he Sam softly.

“Hi” Molly blushed, looking down.

“Do you want to come in?” Molly walked in. 

“I’m Molly” she spoke.

“Sam. It’s very nice to meet you, Molly” He stuck out his hand and she shook it.

“I’m a bit nervous. I’ve never done this before.”

“That’s okay. We will take your temperature and get you in a diaper, then I will hold you.”

“Okay.”

“Can I give you a hug?”

“Yeah” she looked up and opened her arms. Sam chuckled a little

“Can I lift you up, honey” 

Molly nodded and Sam lifted her up in his arms and she wrapped her legs around his waist. He held her tight. Sam rubbed a hand up and down her back.

“Thank you” she whispered.

“You’re welcome. Such a good girl. How about we get you in a diaper?” 

Sam carried Molly to his room, he really liked that his roommate was gone every weekend. Sam placed her down on his desk which he set up as a changing table. He placed her down and held her hands.

“I know that this is a bit scary huh, meeting someone new?”

“Yeah” Molly blushed.

“I will go slow, okay. I will tell you what I’m doing, okay.”

“Okay” she smiled

Sam reached into his pocket and pulled out white latex gloves, Molly’s face lit up and he smiled at her reaction. Sam slipped them on and then stroked her cheek, Molly leaning into his touch. She tapped her jeans and Sam nodded, undoing her button and zipper. She took off her flip flops and Sam pulled down just her jeans and she stepped out of them. 

“Good girl” he smiled. “Can you sit on the table for me?” Molly nodded.

She sat on her the table and Sam grabbed the lube and rectal thermometer. She blushed and laid down on her back, legs up and Sam placed the lubed and thermometer down and pulled her under pants off, noticing that she’s shaved herself and he grabbed the lube.

“I’m going to take your temperature, thank you for getting in position.” 

Sam praised and he squirted some lube on his forefinger, rubbing it, before lighting brushing against her tight hole. Sam slowly inserted the thermometer, holding it there. Sam lightly touched her pussy lips, spreading them a bit.

“This is making you wet, sweetheart.” 

“Yeah” she smiled.

“I’m glad.” He said pulling out the thermometer and stripping off the glove, pulling on a new on.

Sam grabbed a pink diaper and opened it up, placing it under her bum. He grabbed wipes and wiped Molly clean. He squirted lotion onto her and rubbed in on her butt and vagina. He grabbed the baby powder and sprinkled it on her lightly. Changing gloves, he did the diaper up and Molly sat up. Sam placed a gloved hand under her chin, his thumb on her chin, opening her mouth a bit.

“Wider please, honey” Sam spoke and Molly opened her mouth a bit more. Sam placed two fingers in her mouth. She wrapped her mouth around and started to suck. Sam rubbed her diaper. “There we go.”

“Mmmm” Molly moaned.

“I’m going to hold you now.”Sam pulled his fingers out of her mouth and pulled off the gloves. He lifted her in his arms.

“Thanks for not being weirded out by this.” Molly said quietly. 

“The diapers and pullups is a little different, but hey, I want to help out anyway I can.”

“Thanks.” 

Sam held Molly and patted her diapered bottom and sat down. He just hled her for the next little while, which is all Molly wanted and needed.


	2. A whole weekend

Molly came over the next weekend, paying for the whole weekend. Sam got his navy blue scrubs on. He had stocked up on my medical supplies. Molly wanted an exam, plus Sam had plans for her, which she liked. 

“Hey, sweetheart” Sam smiled, lifting her in his arms and closing the door.

“Hi” she blushed. Sam rubbed a hand on her back.

“How are you honey?” he asked and she nuzzled closer to him.

“Good. How are you?”

“I’m good. Are you ready for your exam?”

“Yes.” 

Sam carried her into the room and put her down. He had the room all set up. He pulled on white latex gloves and went to help take her clothes off. He pulled off her shirt and unhooked her bra. Next Sam undid her jean buttons and looked up smiling. Molly blushed more.

“What a goof girl you are wearing a pullup.” He praised undoing the zipper and pulling her jeans off. Molly stepped out of them. He cupped her cheek with his gloved hand and kissed her. “Spread your legs for me please.” 

“Yes doctor” Sam rubbed between her legs on the pullup. 

“How do you feel wearing them out in public?” he asked voice almost clinical. 

“Good. A little embarrassed, but no one can tell.” 

“And you don’t wet them?”

“No.”

“Good girl.” Sam stopped rubbing and pulled them down and Molly stepped out of them. “I’m going to have you lay on the bed, feet planted.”

Molly did as she was instructed and Sam grabbed the rectal thermometer which was huge and put lube on it. He had a stool ready and sat on in. He slid the thermometer in her bum. Molly sort of pushed it out.

“Sorry” she said and he chuckled a bit.

“That’s okay, sweetheart. It happens”

A few minutes later, Sam pulled it out and nodded. He cleaned it and put it away. He grabbed his stethoscope. Instructing Molly to sit up. He listened to her heart and lungs then had her lay back down.

“I’m going to examine you now.”

Sam sat on the stool while she laid down. He helped spread her legs, his gloved hands rubbing her inner thighs. He lightly touched her pussy and spread it open. 

“How often do you masturbate?” his thumb lightly brushed her clit.

“Um… once a day” she admitted .

“How many times do you usually cum?” Sam parted her lips with one hand and saw how soaked she was.

“Two or three times. Oh!” she gasped as he inserted a finger.

“Do you use toys of your fingers?” 

“Toys.”

“And how often are they in a diaper or pullup.” He inserted two fingers and pushed on her stomach to check her ovaries.

“Usually pullups or diapers.”

“Very good.” Sam pulled out his fingers and changed his glove on his right hand squirting some lube.

Sam inserted a finger in her vagina and rectum, rubbing a hand on Molly’s inner thigh. Sam pulled out and stripped his glove off.

“Everything feels good Molly. I’m going to check your mouth now. Gag reflexes. 

Sam took off his other glove, donning new ones, blue this time. He had her sit up, he caressed her face with the back of his hand. Molly smiled and then opened her mouth. Sam gripped her chin, holding her mouth open.

Sam inserted a finger into Molly’s mouth and going lightly to touch the back of her throat. He pulled away for a moment and then did it again. Sam pulled her finger out, still keeping his other hand on her chin. He inserted two fingers this time.

“Very good, sweetheart. You’re doing well” he said, fingers still in her mouth. “Just going to feel around, almost done” he half cooed.

When Sam was finished, he pulled his fingers out and caressed her face with his other hand for a moment. Molly leaned into his touch and Sam leaned forward, kissing her forehead.

“Very good, honey. The first part of the exam is done.” 

“First part, doctor?” she asked.

“Yes, it seems that you use toys only to masturbate. So, I’m going to masturbate you, while you wear a pullup. Get you used to fingers.” This made Molly blush. 

“Okay.”

“Such a good girl” Sam smiled. “I’m going to put on some purple gloves to get you back in your pullup, then I’ll be wearing white for the treatment.”

The way he spoke made Molly more and more aroused. Sam quickly got her in a pullup, rubbing her a bit. Sam stripped the purple gloves off, pulling white ones on.


	3. Chapter 3

Sam had Molly laying down on the bed and had her pullup off. The petite girl was so wet and Sam smiled seeing her arousal. He had his medical mask on with his white latex gloves and scrubs. He took his left hand, thumb brushing against her lip, Molly parted her lips. Sam stuck his thumb in and she started to suck. With his right hand he reached between her legs and gave a spank to her inner thighs and she spread her legs. He started to rub her clit. 

Molly focused on his fingers between her legs and moved her left leg up to give him more access. Sam pulled his thumb out of her mouth and grabbed the lube. She poured some on his right hand, rubbing his fingers together. He placed his thumb back in her mouth with his left hand and went back to rubbing between Molly’s legs.

Sam slowly slid a finger in, his hand in her mouth, now roaming her body. He moved his finger in and out, Molly gasped, arching her back as his other hand worked her breasts. Sam inserted two fingers in, thumb going back in her mouth, he rubbed his hand over her vagina and her moans made Sam happy.

He worked two fingers in again, rubbing her clit with his thumb. He moved his left hand from her mouth to her neck. Not squeezing, just making sure she knew he was in control. Molly closed her eyes, letting the sensation come over her and she came. Sam’s hand on her throat, goes to stroking her cheek and rubbing her pussy to bring her down. 

“Good girl, Molly” Sam praised.

“Thank you, doctor” you whispered. He lightly spanked her pussy.

“Up, on all fours. Your treatment is not done.”

Molly turned around on all fours, spreading her legs. Sam used both gloved hands spread her ass and vagina. He rubbed her pussy. Molly got on her elbows. He placed two fingers into her while the other hand rubs her back. Sam reached over and grabbed a thermometer and inserted the thermometer into her ass while working his fingers in and out. He pulled his fingers out and rubbed her. Sam pulled the thermometer out.

“Turn over, sit up and spread your legs.” Sam’s tone was clinical and Molly looked a little worried as Sam stripped the gloves off. Sam grabbed new gloves and looked at Molly. “Oh, sweetheart, I’m sorry. I didn’t mean to sound that clinical.”

“It’s okay.” she whispered.

“No, it’s not sweetie. You took your treatment so well. You came with my fingers and not a toy, that is very good. That is what we wanted.” Molly nodded.

“Can-Can I wear a diaper?”

“Yes, honey, absolutely.” I’m going to clean you up. I’m really proud of you.” 

“Yeah?” Molly asked.

“Yeah. So, so proud of you.” 

Sam placed the white gloves down and grabbed blue ones, pulling them on. He took the mask off and kissed Molly’s forehead, stroking her cheek. He went and warmed up water and got a wash cloth, wiping Molly down, praising her the whole time. He got a dry towel and wiped her dry.

Sam slipped the blue gloves off and don white gloves, grabbing the supplies he needed to diaper her. He opened the pink diaper, her legs lifted up and slid it under her bum. He smiled as he spread her legs and grabbed lotion rubbing it over her.

“Oh” she gasped.

“Aw, sorry. You’re still pretty sensitive, huh?” he said and she nodded. He sprinkled the powder and then changed his gloves and did the diaper up, rubbing it a bit and giving her a few pats. “There we go, Molly. You’re safe. You’re loved.”

Sam lifted Molly up in his arms, grabbing a blanket and wrapping it around her.


	4. Chapter 4

Molly was back she was a little nervous, because Sam had been good with her, encouraging her to wear the pullups more, but her stomach was upset. She hadn’t gone to the bathroom in two days. Sam opened the door wearing his navy blue scrubs and Molly stepped in, looking down a bit. Sam smirked, knowing something was up. He placed a finger under her chin, lifting his head up.

“Molly, is there something you’d like to tell me?” he said. 

“Yes” she squeaked out.

“Go on” he noticed she started blushing.

“I haven’t gone to the bathroom, in two days. I don’t mean…pee... I mean…”

“I know what you mean. Alright, time for an exam so I can determine the course of treatment you need.”

She whined and he chuckled, lifting her up in his arms and holding her tight. She was in a skirt and when Sam rubbed her bottom he smiled noticing her pullup. He carried her in and placed her down.

“Please undress for me, leaving your pullup on.” he instructed

“Yes doctor” Molly blushed.

While Molly undressed Sam pulled up the medical tray and pulled out all the supplies he needs. He placed the medical mat on desk and molly and stood there ready. Sam smiled at her and reached for his white latex gloves and pulled them on and his medical mask. He told Molly to may on her back with her feet on the table, knees bent. Sam pulled off the pullup and grabbed the thermometer. 

“I’m going to start by taking your temperature. I will then palpitate your stomach, followed by a digital rectal exam and we will see where to go from there.”

Molly nodded. Sam squirted some lube on the thermometer and rubbed it and slid it in, holding it there. Molly blushed, she was so embarrassed. Sam pulled the thermometer out and nodded, placing it down. He gently felt around her stomach, circling and tapping. Molly winched and Sam paused looking up at her. 

“Molly. You feel very blocked.” Sam said and she blushed. “You did the right thing by telling you, sweetheart”

Sam squirted lube on his index finger and placed a hand on the inside of her thigh and lightly rubbed her hole, sliding his finger in and feeling around. A minute later, Sam pulled his finger out and nodded to himself, before looking at Molly.

“Alright, sweetheart. You are backed up. I’m going to administer two suppositories and we will see if that helps. Then, if you’re still backed up I am going to give you an enema.”

“Nooo” Molly whined.

“I’m sorry, honey. But you need this. I know your tummy hurts.” Molly nodded.

Sam unscrewed the lid and grabbed the lube and coated the first suppository and pushed it against her hole, sliding it in and holding it there with his finger. Molly whined, tearing up a bit.

“I know it burns, honey, but its’ going to make you feel better.” Sam cooed. 

He grabbed the second one. Lubed it and slid it in and held it there, waiting for it to melt. Sam pulled his finger out and Molly whimpered.

“I need you to hold it for me.” Sam changed his gloves. “You need to hold it for as long as you can. I’m going to set the timer for fifteen minutes.”

“Yes doctor” Molly whimpered. Sam walked over and set the timer, walked by her cheek, stroking her cheek with his gloved hand. “there we go sweetie. You’re safe.”

“Do I get to use the toilet?” Molly asked looking over at him.

“Oh yes, of course.” Sam said, kissing her forehead.

The timer dinged and Molly looked at Sam he nodded and she went to the bathroom. Sam waited two minutes before entering. Molly looked at him and Sam brought in the baby wipes. He handed them to Molly and let her wipe herself. 

Once she was finished Molly washed her hands and Sam lifted her in his arms. He held her tight, he swayed side to side and carried her back to the table and laid her down. He held her hand and stroked her cheek.

“I’m going to give your bottom a little break.”

“I feel better” he whispered.”

“That’s good. I still need to do another digital exam to see if you need enema.”

Half an hour later, Molly had drifted off to sleep and Sam lightly kissed her forehead and calling her name. Molly opened her eyes and giggled. She rolled on her back and Sam grabbed the lube and positioned himself between her legs and inserted a finger.

“Alright, Molly. You feel really good, sweetheart. You wont need an enema right now.”

Sam pulled his finger out and pulled his gloves off, pulling new ones on and grabbing a diaper. Molly raised her legs as Sam slid the diaper under her and grabbed the lotion, he rubbed it over her and grabbed the baby powder, sprinkling it on. He did the diaper up and pulled his gloves off and lifted Molly up.

**Author's Note:**

> comment and kudos


End file.
